1. Study the target molecule and the list of available reagents. CH 12-4: Performing a Grignard Synthesis-II From the reagent list (stockroom) identify the reactants needed to make the target molecule. Step #1: React alkyl halide with Mg in ether to make Grignard Reagent. Step #2: React Grignard reagent with an aldehyde, ketone, ester, or epoxide. Step #3: Acid/base neutralization. Locate the new bond in the target molecule and draw a “dot” on the alcohol carbon. Which reactant will you use to make the Grignard reagent? Convert to an alkyl halide, if necessary. Is the target a 1 o, 2 o, or 3 o alcohol? Do you need an aldehyde, ketone, ester or epoxide? If symmetrical alkyl groups at the alcohol carbon, then use an ester.

2. Grignard Example #1 (ketone  3 o alcohol) (3 o alcohol)

3. Grignard Example #2 (aldehyde  2 o alcohol) (2 o alcohol)

4. Grignard Example #3 (ester  3 o alcohol) (3 o alcohol)

5. Grignard Example #4 (epoxide  1 o, 2 o, or 3 o alcohol) R=R’=H (1 o alcohol) R=H, R’=alkyl (2 o alcohol) R=R’=alkyl (3 o alcohol)